SYNTHESIS OF AMINO ACIDS FROM SUBSTITUTED CYANOACETIC ESTERS

1950 ◽  
Vol 28b (7) ◽  
pp. 352-357 ◽  
Author(s):  
Paul E. Gagnon ◽  
Jean L. Boivin ◽  
Jacques Giguere
Keyword(s):  
Amino Acids ◽  
Low Temperature ◽  
Hydrazine Hydrate ◽  
Nitrous Acid ◽  
Hydroxybutyric Acid ◽  
Cyanoacetic Ester

The Darapsky method has been successfully applied to the synthesis of aminoacids from substituted cyanoacetic esters, RCH (CN)COOC2H5. R=CH3CH (CH2)4CH3, CH3CH(CH2)5CH3, CH3(CH2)11, HOCH2CH2, o-ClC6H4CH2, p-CH3C6H4O(CH2)2, p-CH3C6H4O(CH2)3, p-C2H5C6H4O(CH2)2, p-C2H5C6H4O(CH2)3, p-ClC6H4O(CH2)2, p-ClC6H4O(CH2)3, p-BrC6H4O(CH2)3. The esters were prepared by condensation of cyanoacetic ester with suitable bromides. When treated with hydrazine hydrate, they gave rise to hydrazides, which were identified by their anisal derivatives. Azides were obtained by the action of nitrous acid on hydrazides at low temperature and were transformed by heating with alcohol into carbethoxyaminonitriles. Finally, the latter by hydrolysis yielded the following amino acids: dl-α-amino-β-methylcaprylic acid, dl-α-amino-β-methylpelargonic acid, dl-α-aminomyristic acid, dl-α-amino-γ-hydroxybutyric acid, dl-α-amino-γ-p-methylphenoxybutyric acid, dl-α-amino-δ-p-methylphenoxyvaleric acid, dl-α-amino-γ-p-ethylphenoxybutyric acid, dl-α-amino-δ-p-ethylphenoxyvaleric acid, dl-α-amino-γ-p-chlorophenoxybutyric acid, dl-α-amino-δ-p-chlorophenoxyvaleric acid, and dl-α-amino-δ-p-bromophenoxyvaleric acid.

Composition chimique de sèves xylémiques du genre Lycopersicon (Solanaceae) en relation avec l'environnement. I. Effet de la température

1990 ◽  
Vol 68 (9) ◽  
pp. 1942-1947 ◽  
Author(s):  
Philippe Brunet ◽  
Bruno Sarrobert ◽  
Nicole Paris-Pireyre ◽  
Ange-Marie Risterucci
Keyword(s):  
Amino Acids ◽  
Low Temperature ◽  
High Performance ◽  
Xylem Sap ◽  
Lycopersicon Hirsutum ◽  
Fresh Weight ◽  
Sensitive Species ◽  
Composition Chimique ◽  
Analytical Processing ◽  
Two Temperature

Two species of tomato, Lycopersicon esculentum Mill. var. EGE12P1 and Lycopersicon hirsutum Humb. & Bonpl. ecotype LA 1777, were submitted to two temperature treatments, 20 or 10 °C. After a short study of plant growth, we analysed the chemical composition (cations, anions, and amino acids) of xylem sap by high performance liquid chromatography. A comparison of fresh weight increase at 20 and 10 °C of both plant species showed that L. hirsutum was the least affected by low temperature. The volumes of secreted sap and the quantities of ions transported showed great disturbances in the sensitive species (L. esculentum), especially in the case of potassium. In xylem sap of both species studied, but only at 10 °C, we noticed the appearance of ammonium. The possibility of contamination during analytical processing was eliminated. Moreover, determinations of amino acids levels showed that ammonium did not arise from degradation of amides present in xylem sap. In any event, the proportion of nitrate absorbed and reduced in roots increased at low temperature; it is much more important in L. hirsutum and could constitute a tolerance factor to low temperatures. Key words: ammonium, low temperature, Lycopersicon, xylem sap.

Changes in Fumitory Achenes During Low Temperature After-Ripening

Weed Science ◽  
1973 ◽  
Vol 21 (4) ◽  
pp. 310-313 ◽  
Author(s):  
Larry S. Jeffery ◽  
John D. Nalewaja
Keyword(s):  
Amino Acids ◽  
Fatty Acids ◽  
Low Temperature ◽  
Ethyl Alcohol ◽  
Longitudinal Section ◽  
Soluble Carbohydrates ◽  
Ripening Period ◽  
Embryo Size ◽  
Moist Sand ◽  
Fumaria Officinalis

Fumitory (Fumaria officinalisL.) achenes were after-ripened in moist sand at 4 C for 0, 15, 30, 45, and 60 days. Embryo size in longitudinal section increased 14 times during after-ripening. The percentage of ether soluble lipids and their fatty acids remained constant during the entire after-ripening period. Soluble carbohydrates were the highest at the 45-day period of after-ripening when embryo growth was rapid. The concentration of 70% ethyl alcohol soluble amino acids increased gradually over the first 45 days of after-ripening and decreased over the last 15 days as embryo growth became more rapid.

scholarly journals HISTOCHEMICAL DIFFERENTIATION BETWEEN TYROSINE AND CHLOROGENIC ACID IN PLANT TISSUES I. NITROUS ACID REACTIONS AND METAL CHELATION OF NITROSOTYROSINE

1968 ◽  
Vol 16 (3) ◽  
pp. 191-198 ◽  
Author(s):  
R. M. REEVE
Keyword(s):  
Amino Acids ◽  
Chlorogenic Acid ◽  
Nitrous Acid ◽  
Metal Chelate ◽  
Ultrastructural Localization ◽  
Plant Tissues ◽  
Metal Chelation ◽  
Copper Chelation ◽  
Acid Reaction ◽  
Color Reactions

Copper chelation of nitrosotyrosine has been found useful for histochemical localization for tyrosine in thick, fresh sections of large celled plant tissues. The nitrous acid reaction for ortho-dihydroxyphenolics also has been found useful for localization of chlorogenic acid, caffeic acid and dihydroxyphenylalanine in plant tissues. Application of these tests separately to serially adjacent sections demonstrated the distribution of tyrosine and chlorogenic acid in different plant tissues. Tests tube reactions on known substances verified specificity and also demonstrated that the presence of other amino acids and phenolics did not interfere with the positive test for tyrosine. The color reactions are sufficiently intense for stereoscopic microscopy and tested sections may be measured photometrically. Further adaptability of the nitrosotyrosine-metal chelate reaction to procedures for ultrastructural localization is suggested.

USE OF KANAMYCIN FOR THE ISOLATION OF AUXOTROPHIC MUTANTS OF ACTINOBACILLUS MALLEI

1966 ◽  
Vol 12 (4) ◽  
pp. 641-652 ◽  
Author(s):  
D. H. Evans
Keyword(s):  
Amino Acids ◽  
Nitrous Acid ◽  
Minimal Medium ◽  
Inhibitory Concentration ◽  
Bactericidal Effect ◽  
Defined Medium ◽  
Chemically Defined Medium ◽  
Auxotrophic Mutants ◽  
Viable Cells ◽  
Minimal Media

Growth of Actinobacillus mallei was inhibited by kanamycin; the minimal inhibitory concentration in a complex medium was 1.25 μg/ml and in a chemically defined medium 5 μg/ml. Higher concentrations of kanamycin had a pronounced bactericidal effect. When a suspension of cells containing 5 × 107 viable cells/ml was incubated in the presence of 20 μg/ml of kanamycin in a chemically defined medium, complete sterilization resulted after 6 hours. Cells irradiated with ultraviolet light were grown in complex or supplemental minimal media, washed, and exposed to 20 μg/ml of kanamycin in minimal medium for 4 hours. Auxotrophic mutants with requirements for tryptophane, phenylalanine, proline, and uracil were detected among the survivors of kanamycin treatment. After treatment with 0.01 M nitrous acid and growth in minimal medium supplemented with amino acids, cells were washed and then exposed to kanamycin in minimal medium. The proportion of autotrophs among the survivors varied from 1.3 to 75%. Mutants with requirements for each of the following amino acids were identified: methionine, methionine or cystine, arginine, leucine, tryptophane, histidme, and proline, with methionine-requiring mutants predominating. Exposure of mixtures of prototrophs and uracil-dependent and methionine-dependent auxotrophs to 20 μg/ml of kanamycin for 4 hours resulted in approximately 700- and 300-fold increases, respectively, in the ratio of auxotrophs to prototrophs.

Effect of temperature on the growth of wheat. III. Chemical constituents of Marquillo, Kenya Farmer, and two dwarf progeny grown at three temperatures

1969 ◽  
Vol 47 (1) ◽  
pp. 35-45 ◽  
Author(s):  
Yun-Te Yao ◽  
David T. Canvin
Keyword(s):  
Amino Acids ◽  
Low Temperature ◽  
Organic Acids ◽  
Chemical Constituents ◽  
Temperature Treatment ◽  
Effect Of Temperature ◽  
Soluble Carbohydrate ◽  
Low Temperature Treatment ◽  
Marked Accumulation

Marquillo × Kenya Farmer wheat dwarfs 1 and 2 were grown at 16 °C (inhibited "grass-clump" habit), at 21 °C and at 26° (normal habit). The parent varieties were grown under the same conditions for comparison.Analysis of the dwarf strains grown at 16 °C revealed that there was no deficiency of soluble carbohydrate, amino acids, organic acids or chlorophyll when compared to the parent varieties or to the dwarf strains grown at 26 °C. Rather there was marked accumulation of most of these substances in the non-growing plants at 16 °C. The results are consistent with the view that the suspension of growth in the dwarf plants is not due to the lack of ability to synthesize organic metabolites but rather that an inhibitor is accumulated during the low temperature treatment that blocks growth by some other mechanism.

Identification and validation of differentially expressed transcripts in a hepatocyte model of cold-induced glycerol production in rainbow smelt (Osmerus mordax)

2011 ◽  
Vol 301 (4) ◽  
pp. R995-R1010 ◽  
Author(s):  
Jennifer R. Hall ◽  
Kathy A. Clow ◽  
Matthew L. Rise ◽  
William R. Driedzic
Keyword(s):  
Amino Acids ◽  
Low Temperature ◽  
Pyruvate Dehydrogenase ◽  
Cdna Array ◽  
Pyruvate Dehydrogenase Kinase ◽  
Osmerus Mordax ◽  
Type Ii ◽  
Glycerol Production ◽  
Rainbow Smelt ◽  
Transcript Levels

Rainbow smelt ( Osmerus mordax ) avoid freezing by producing antifreeze protein (AFP) and accumulating glycerol. Glyceroneogenesis occurs in liver via a branch in glycolysis and gluconeogenesis and is activated by low temperature. Hepatocytes were isolated from the livers of fish acclimated to 8°C. Cells were incubated at warm (8°C; nonglycerol accumulating) or cold (0.4°C; glycerol accumulating) temperature over a 72-h time course. Reciprocal suppression subtractive hybridization libraries enriched for cold-responsive transcripts were constructed at 72 h. Microarray analyses using a 16K salmonid cDNA array were performed at 24, 48, and 72 h. Expression of type II AFP and 21 carbohydrate, amino acid, or lipid metabolism-related transcripts were validated using quantitative RT-PCR. Type II AFP transcript levels were not directly temperature related. In cold cells, levels of the glucose synthesis transcript were transiently higher. Increased glycerol production was not associated with increased phosphofructokinase or cytosolic glycerol-3-phosphate dehydrogenase transcript levels. Levels of transcripts (phosphoenolpyruvate carboxykinase, mitochondrial malate dehydrogenase, alanine aminotransferase, glutamate dehydrogenase, and aquaglyceroporin 9) associated with mobilization of amino acids to fuel glycerol accumulation were all transiently higher, suggesting a common regulatory mechanism. In cold compared with warm cells, pyruvate dehydrogenase kinase [an inhibitor of pyruvate dehydrogenase (PDH)] transcript levels were 20-fold higher. Potent inhibition of PDH would direct pyruvate and oxaloacetate derived from amino acids to glycerol, as opposed to oxidation via the citric acid cycle. Levels of a transcript potentially encoding glycerol-3-phosphatase, an enzyme not yet characterized in any vertebrate species, were higher following cold incubation. Finally, this study also presents the novel finding of increased glutamine synthetase transcript levels in response to low temperature.

The Reaction of Amino Acids and Proteins with Diazonium Compounds. I. A Spectrophotometric Study of Azo-Derivatives of Histidine and Tyrosine.

1952 ◽  
Vol 5 (4) ◽  
pp. 736 ◽  
Author(s):  
HG Higgins ◽  
D Fraser
Keyword(s):  
Amino Acids ◽  
Nitrous Acid ◽  
Spectrophotometric Study ◽  
Maximum Absorption ◽  
Direct Reaction ◽  
Quantitative Investigation ◽  
Conjugated Systems ◽  
Azo Derivatives ◽  
Derivatives Of ◽  
Yellow Compound

The coupling in alkaline solution of free histidine and tyrosine with p-diazobenzene-sulphonic acid has been studied as a basis for quantitative investigation of the behaviour of proteins in the presence of diazonium compounds. Both mono- and bisazo- derivatives may be formed with each amino acid, the wavelengths of maximum absorption being 380 and 490 mμ respectively for histidine and 325 and 480 mμ respectively for tyrosine ; the wavelength displacements on accepting a second diazonium group are comparable to effects reported for similarly conjugated systems. When appropriate corrections are made for other absorbing components, the extinctions at 490 mμ and the initial histidine concentrations up to the (bis) equivalent of diazonium compound conform to Beer's law, showing that bis(azobenzenesu1phonic acid)histidine is formed exclusively under these conditions. At higher histidine concentrations mono(azobenzenesulphonic acid)histidine is formed in increasing proportions. Even at low initial tyrosine concentrations both mono- and bis(azobenzenesulphonic acid)-tyrosine are formed, although mono-coupling is again favoured more as the concentration increases. No direct reaction between histidine and the nitrous acid used in the formation of the diazonium compound could be detected spectrophotometrically, but diazotization of tyrosine appears to reduce the propensity for bis-coupling to some extent. If urea is incorporated in the system to destroy excess nitrous acid, a yellow compound having maximum absorption at 430 mμ is formed between p-diazo-benzenesulphonic acid and the urea.

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